This post is part of a series I’ve done on Route 66. In 2022, I drove the entirety of Route 66 from Chicago to Los Angeles. 2500 miles, 8 states, countless stories, and an endless stretch of small towns, neon, diners, motels, and roadside attractions. Read through all of my Route 66 posts here. They’re also linked at the end of this post. If you’re planning your own Route 66 road trip, either the whole thing or just a part, I hope these help you out. Enjoy the drive!

It’s always a bit exciting setting out on a road trip, but since Route 66 is the ultimate American road trip, it feels extra special. Loading up the car and pulling out of Chicago to set out across the country…2500 miles to California…a trip that many people before you have experienced…some out of necessity and some just for the adventure of hitting the road. I’m ready to go just thinking about it!

If you’re driving Route 66 from Chicago to Los Angeles and you’re anything like me, you’re probably going to want to break the whole trip into smaller segments to make the planning a little easier. Well, the first major segment of the trip is from Chicago to St Louis and there’s a LOT here. 

Growing up on Route 66 (Tulsa) and just having a general sense of travel through the US, I always thought more heavily of the New Mexico and Arizona stretch of Route 66 than the beginning portion that winds through the midwest. But after driving Route 66 through Illinois (it was my first time in Illinois – I’d never even been to Chicago!), I can say that I was pretty impressed by everything I saw. 

Being from Oklahoma, I thought I knew farmland (ha!), but what you see driving through Illinois is unlike anything else. Mix that with Chicago (there’s so much to see!) and a pretty high concentration of attractions along the route (museums, charming small towns, historic restaurants, plus all of the Lincoln sites in Springfield) and you’ve got the recipe for a fantastic start to your Route 66 road trip. 

Route 66 Chicago to St. Louis

This post is going to read a bit like a travel diary of my Route 66 going westbound from Chicago to St. Louis. I’ll include all of the stops I made (plus others I didn’t have time for or they were closed) in the order that you’ll come to them and sooooo many pictures. 

***And a little disclaimer before we get started: check hours and days of operations to attractions, restaurants, etc. to places that you’re interested in before you go because not everything is open 24/7 and it’s always a bummer to miss something you were really looking forward to when you couldn’t shuffled things around a bit to make it happen. 

Let’s get this party started!

Route 66 Downtown Chicago to Joliet

I’ve written a whole separate post about Route 66 in the Chicago area (downtown Chicago to Joliet) that you can read here, but below I’ll include my highlights from that stretch to get you started. 

Route 66 Beginning Sign: Downtown Chicago

If you only have time for one stop in Chicago, this is the one you definitely can’t miss. You’ve got to have that photo opp at the start of your adventure!

Lou Mitchell’s & The Berghoff: Downtown Chicago

Both Route 66 icons operated for 100+ years, Lou Mitchell’s is open for breakfast and lunch while Berghoff does lunch and dinner (plus check which days each is open). You’ve got to eat at one or the other at least. 

Route 66 Welcome Center: Joliet, IL 

This is your first official Route 66 visitors/welcome center so it’s worth a stop. I got an early start leaving Chicago so it wasn’t open when I came through, but it looks really nice. 

Leaving Chicagoland Behind: Onward Across the Midwest!

Gemini Giant at the Launching Pad: Wilmington, IL

This is my favorite of the giant “Muffler Men” along Route 66 so far. The Launching Pad was closed when I came through here, and I’ve heard that they’re not going to be able to reopen as a restaurant anytime soon, but are going to be running the gift shop regularly. 

Polk-a-Dot Drive-In: Braidwood, IL

Also closed when I came through, but this looks like a pretty authentic 50s style diner (mini jukeboxes on the tables, etc). 

First National Bank: Dwight, IL

Designed by famous architect Frank Lloyd Wright, the area where the bank sits in downtown Dwight is worth getting out to stretch your legs. 

Historic Ambler/Decker Station: Dwight, IL

This is such a great restored service station. During the summer travel season, the inside is open 10am-2pm Wednesday to Sunday. 

Standard Oil Company: Odell, IL

Here’s a double whammy for you! Two charming, well preserved service stations back to back!

Pontiac: Illinois’ Cutest Little Route 66 Town

Pontiac is a MUST STOP on Route 66. I personally command it. It has super cute small town vibes, a darling little square, and some of my favorite museums along the route. 

Meramec Caverns Barn: Pontiac, IL

I’m actually embarrassed to say how much time I’ve spent looking for Meramec Caverns barn signs along Route 66 haha. But this is a good one! Technically in Cayuga, you’ll see it on the right side of the road (going westbound) coming into Pontiac. 

Old Log Cabin: Pontiac, IL

I’ve eaten in a lot of roadside dives along Route 66, but so far this is the best burger I’ve had. It’s charbroiled and oh so delicious. 

Route 66 Illinois Hall of Fame: Pontiac, IL

Okay, I heard a loooooot about this place in all of my research and in my mind I thought it was going to be like the Oklahoma Route 66 in Clinton (new and shiny, Smithsonian quality, top notch exhibits)…well, it’s not…but it’s completely charming. 

Located in a historic brick fire station, it has more small town historical society museum vibes (item descriptions typed up by volunteers, items displayed in old trophy cases, not sure if you’re in a museum or flea market, etc), but in the best way possible. 

First of all, I love a museum where the building is almost as interesting as the items themselves. Well this place is a complex. The Route 66 Illinois Hall of Fame is located in a pretty big room on the bottom floor and then you go upstairs and it’s a complex of smaller museums (some of them just a room or two). 

So there’s a lot to see here, but the absolute don’t miss is Bob Waldmire’s VW van. Bob is a Route 66 icon (an artist who spent much of his life traveling back and forth on Route 66 documenting what he saw) and the inspiration behind the Fillmore character in the Pixar movie Cars. 

I also really loved the part upstairs where they recreated a home from the 1940s. 

And the best thing about this place…it’s FREE! I love being able to poke around and decide if I’m in and out really quick or want to stay a while without having to decide if it’s worth paying to go in or feel like I have to get my money’s worth once I’m inside. 

Also don’t miss the alley/parking area behind the museum because there’s a lot to see back there. And there’s a pretty sizeable free parking lot across the street. 

Pontiac Oakley Automobile Museum: Pontiac, IL

So far this has been hands down my favorite car museum on Route 66 and I’m sure it’s partly the building. Located on the town square, it’s a historic building that still has the original flooring, tin ceilings, and dark wood paneling. Add all of the cars and little vintage vignettes and it’s SUCH A COOL PLACE. 

It’s also free. 

Let’s Keep on Cruising Towards Springfield

Memory Lane: Lexington, IL

There are two memory lane type stretches in the area and the one in Lexington is the first one you’ll come to. There’s a pretty visible sign so you’ll know where to turn off the road. It’s only a mile or so and it’s pretty heavily wooded stretch so you won’t see it from the main road. Honestly, there’s not a ton to see here (just a few signs really), but you can drive it in your car so you might as well. 

Towanda Route 66 Parkway: Towanda, IL 

The parkway in Towanda is the really good one. And unfortunately I was short on time when I drove through here so I didn’t get as many photos as I’d like. This stretch of old 66 is not open to cars, but you can walk or bike it (although you can see the whole thing while you drive by). It has some pretty cool signs and setups including Dead Man’s Curve and the best sets of Burma Shave signs I’ve seen anywhere on the route. 

Sprague’s Super Service: Normal, IL

Another great refurbished service station that’s definitely worth your time. I peeked through the windows and it looks like a really good gift shop inside too. 

Cruisin’ with Lincoln on 66 Visitors Center: Bloomington, IL

This place is basically the lobby of the McLean County Museum of History, but there’s some pretty good exhibits to read and a great gift shop. It’s free to stop in and this is where I ended up getting my Route 66 passport (they also had them at the Joliet Route 66 Welcome Center-closed when I was there- and the Route 66 Illinois Hall of Fame-credit card machine was down). 

Funks Grove Pure Maple Sirup: Funks Grove, IL

They had closed up shop for the day when we drove through, but if it’s open, stop and get some maple sirup to take home with you. 

Historic Downtown: Atlanta, IL

Besides Pontiac, this is my favorite little town in Illinois. It’s pretty picturesque and photo ops abound. Don’t miss the Hot Dog Muffler Man and the Palm Grill Cafe sign (currently Missy’s Sweet Shop). 

J.H. Hawes Grain Elevator & Museum: Atlanta, IL

You used to be able to tour the fully restored wooden grain elevator (the only one in Illinois), but there’s still plenty to see outside on the property. 

World’s Largest Covered Wagon: Lincoln, IL

This is a roadside attraction at its finest. 

Postville Courthouse: Lincoln, IL

A replica of the 1840s courthouse where Lincoln practiced law for a while. It does have limited hours where you can tour the inside, but you can really see a lot from the outside. 

The Tropics Restaurant: Lincoln, IL 

Such a great looking neon sign and I can’t believe I missed it!

Entering the Land of Lincoln: Springfield, IL

Boy oh boy there’s a lot here. Surprisingly (or not), Springfield, IL was one of the stops I was most excited about. I think because I’ve spent time in the states and cities along the route in Missouri, OK, TX and NM many times before but Illinois was brand new to me and there’s so much history here. 

If you’re a history buff, you’re going to want to carve out some extra time to spend around Springfield. 

Cozy Drive In: Springfield, IL

I singled this out as my must eat place in this section of the route (it’s a rule that you have to eat at least one greasy/fried meal a day when you’re driving Route 66 ; ) and honestly the food was just okay, but it’s a really cute place with a lot of history (and plenty to read about different places inside). 

Dana Thomas House: Springfield, IL

I’m a Frank Lloyd Wright fan so I’ll usually go out of my way to see a house or building of his, and this one is pretty incredible although I was so sad I didn’t have time to do a tour of the inside. 

Rail Splitter Statue: Springfield, IL

I just happened to be in Springfield when they were setting up for the state fair and WOWZERS. It’s on my bucket list to go to a big time midwestern state fair so maybe I’ll got back to Springfield for this one. Whether you’re in town for the fair or not, you’ll want to see the Rail Splitter statue at the fairgrounds. 

Route 66 Drive In: Springfield, IL

There aren’t too many drive-ins left in the country so it’s always nice to see one still standing. And what a way to spend a summer evening!

Illinois State Capitol (Old & New): Springfield, IL

The Illinois State Capitol is pretty stunning and there’s an opportunity for a cool photo op with the Route 66 sign on the street out front. If you have time, I’m sure it’s worth going inside or doing a tour. The Old State Capitol is also in the area and something you’ll want to see especially if you’re interested in all of the President Lincoln sites (it’s where Lincoln laid in state in Illinois after he died before he was buried).

Lincoln Presidential Library & Museum: Springfield, IL

This was probably my #1 thing I wanted to do in Illinois and boy, it didn’t disappoint! I am a huge fan of Presidential libraries and will go out of my way for one so I planned a little extra time in Springfield for it. It’s a don’t miss for me…plan to spend at least a couple of hours here. 

Read this post for more information on all of the Lincoln related sites in Springfield and across Illinois.

Lincoln Home National Historic Site: Springfield, IL

I don’t know exactly what I was expecting this to be, but I was BLOWN AWAY by what it actually is. I guess I thought they’d have Lincoln’s home preserved on a little lot in the middle of downtown Springfield, but it’s basically the entire neighborhood. Multiple blocks (including all of the homes, sidewalks, roads, trees, etc.) around the home have all been preserved so you can actually walk the streets and feel like it’s 1860. 

I didn’t have time to actually tour the inside of the home (timed tickets are spaced throughout the day) and it was still 100% worth going. 

Lincoln Tomb: Springfield, IL

I didn’t have time to visit Lincoln’s tomb, but it’s just outside of Springfield in Oak Ridge Cemetery. 

South to St. Louis!

Heading towards St. Louis from Springfield, there are two different alignments that you’ll have to choose from. They both converge just north of Hamel. One follows I-55 pretty closely so I chose to do the route through Chatham, Auburn, Carlinville, Gillespie and Staunton. It’s probably a better drive, but that means you’re going to bypass Litchfield, Mt Olive and Livingston, which all had spots that I wanted to see. 

I was able to do one route driving up to Chicago and the other driving home, but assuming you’re only driving this one way, I think I would focus on plotting out the sites you’d like to see and then chart a course that kind of bounces back and forth between the two routes (it’s doable). 

Basically, I’d drive south through Carlinville then make your way over to Litchfield and down to Livingston (if you want to see the antique mall) but detour for the Rabbit Ranch in Staunton and then connect back up in Hamel. 

I’ve listed the stops below more or less in that order. 

Sugar Creek Covered Bridge: Chatham, IL

Okay, this isn’t technically a Route 66 stop (it’s several miles off the route), but it’s old timey and I had never seen a bridge like this before so it was definitely worth the detour for me. 

Original Brick Road: Auburn, IL

 

Now, I don’t really freak out about original alignments, well preserved stretches of 100 year old pavement off in the weeds, etc. BUT I believe this is the only remaining driveable portion of Route 66 that’s actually brick. And that’s pretty cool. You’ll want to make sure you hit this for sure. 

Deck’s Drug Store: Girard, IL

This place looked super cute and I’d definitely plan a stop next time I’m through here. 

Turkey Tracks on the Route: Girard, IL

You’re going to think I’m crazy, but this just might have been my absolute favorite Route 66 stop in Illinois. I’d read about this in one of my guidebooks and it felt like we were on a wild goose chase down old country roads surrounded by cornfields looking for turkey tracks, but when we saw this we just burst out laughing. 10/10 don’t miss!

Macoupin County Courthouse: Carlinville, IL

Carlinville has the bones to be a magnificent little town, but it could use some TLC. The Macoupin County Courthouse sure is a stunner though!

Litchfield definitely deserves a sizeable stop 

Ariston Cafe: Litchfield, IL

One of the oldest continuously operated restaurants along Route 66 (since 1924!), this is a great place to stop if you want the Route 66 history but more options than the usual greasy burger joints. 

Jubelt’s Bakery & Restaurant: Litchfield, IL

In business since 1922, besides all the legendary sweets, they are a full service restaurant with plenty of options like soups, salads, and sandwiches besides the diner classics. 

Litchfield Museum & Route 66 Visitors Center: Litchfield, IL

Great museum on the inside, great neon on the outside!

Skyview Drive-In: Litchfield, IL

Another classic drive-in on Route 66 and one of the few places you’ll find something to do after dark in small towns like these. 

Carnegie Public Library: Litchfield, IL

Originally built in 1904 with a $10K donation from the Carnegie Foundation (Andrew Carnegie donated $60 million dollars to fund a system of 1600+ libraries across the country), the building is really something to see and it sits in the town square which is pretty cute. 

Soulsby Service Station: Mt. Olive, IL

One of the few restored Shell stations that I remember seeing along the route. 

Pink Elephant Antique Mall: Livingston, IL

As someone who enjoys spending a considerable amount of time rummaging through antique malls, flea markets, and vintage shops, I’ve really enjoyed all the good ones you find along Route 66, but the Pink Elephant Antique Mall has got to be the one that feels most like an attraction. 

And actually, while I was looking around I noticed a couple of families from other countries that seemed to be enjoying looking around almost like they were in a museum or roadside attraction instead of a shop. And really, it all seems pretty distinctly American so if you’re looking for an “experience” (especially if you’re from another country), I would recommend a stop here over pretty much every other antique mall or shop along the route. 

Henry’s Rabbit Ranch: Staunton, IL

Henry’s mostly retired these days so call ahead to schedule an appointment or take your chances just stopping by, but even if he’s not around there’s plenty to look at on the property. 

Many people are a little disappointed to learn that the rabbits are actually VW Rabbits half-buried Cadillac Ranch style (although I’ve heard that maybe there are also furry rabbits inside that he’ll show you if he’s home).

Weezy’s: Hamel, IL

Originally opened as the Tourist Haven in 1938, this little roadhouse has been serving up good food ever since. Famous for their fried chicken, I would also recommend the catfish. 

Route 66 Creamery: Hamel, IL

Wash your heavy, fried meal at Weezy’s down with a creamy custard concrete ; )

Luna Cafe: Granite City, IL

Rumored to be a hangout of Al Capone (but seriously where hasn’t Al Capone been?), they’ve got a great neon sign. 

Chain of Rocks Bridge: Illinois to Missouri

I’ve gushed about the Chain of Rocks Bridge plenty in this post, but basically, I think walking across the Mississippi River on the Chain of Rocks Bridge is a don’t miss. 

St Louis, MO

Yay! You’ve made it to St. Louis! Check out this post for all of my favorite Route 66 stops in the St. Louis area.

Planning a Route 66 road trip? I’ve got all of the info you need! 

I’ve written about my cross country road trip pretty extensively section by section. Read them all here: Part 1 (Chicago), Part 2 (Chicago to St. Louis), Part 3 (St. Louis), Part 4 (St. Louis to Springfield MO), Part 5 (Springfield, MO), Part 6 (Springfield, MO to Tulsa), Part 7 (Tulsa), Part 8 (Tulsa to OKC), Part 9 (OKC), Part 10 (OKC to Amarillo), Part 11 (Amarillo), Part 12 (Amarillo to Albuquerque), Part 13 (Albuquerque), Part 14 (Albuquerque to Flagstaff), Part 15 (Flagstaff), Part 16 (Flagstaff to San Bernardino), Part 17 (Los Angeles). 

Plus I’ve done roundups by state: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, California.

I’ve got the scoop on where to stay including the best Route 66 motels recommendations. 

And finally, my final trip recap where I spill the beans on how many days you need, the best itinerary, my favorite don’t miss spots, and other tips.